4,5-Diamino-2,6-dimethylthiopyrimidine | 61772-85-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,5-Diamino-2,6-dimethylthiopyrimidine
• 英文别名: 2,6-bis(methylthio)pyrimidine-4,5-diamine；2,6-Bis(methylthio)-4,5-diamino-pyrimidin；2,6-bis-methylsulfanyl-pyrimidine-4,5-diamine；2,6-bis-methylsulfanyl-pyrimidine-4,5-diyldiamine；2,6-Bis-methylmercapto-pyrimidin-4,5-diyldiamin；2,6-Bis(methylsulfanyl)pyrimidine-4,5-diamine
• CAS: 61772-85-8
• 化学式: C₆H₁₀N₄S₂
• 分子量: 202.304
• InChiKey: IXZUCRGIXBNBTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-Diamino-2,6-dimethylthiopyrimidine 在 sodium methylate 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 25.5h， 生成 2-Methylthio-4-morpholino-7-methoxy-8-ethyl-7,8-dihydropteridine
  参考文献：
  名称：

  叠氮阳离子的反应。5.在碱的存在下，将水和甲醇添加到1，4-重氮阳离子中。一加合物和二加合物的平衡常数和PMR光谱

  摘要：

  DOI：

  10.1007/bf00473492
• 作为产物：
  描述：

  2,6-bis-methylsulfanyl-5-nitro-pyrimidin-4-ylamine 在 甲醇 、 镍 作用下， 生成 4,5-Diamino-2,6-dimethylthiopyrimidine
  参考文献：
  名称：

  Purines. III. The Preparation of Certain Purine and Triazolopyrimidine Derivatives¹

  摘要：

  DOI：

  10.1021/ja01649a022

文献信息

• Synthesis and screening of 8-(4'-thiazolyl)purines
  作者：A. Giner-Sorolla、J. T. Segarra、M. H. Brooks

  DOI：10.1021/jm00202a006

  日期：1978.4
• The discovery of purine-based agents targeting triple-negative breast cancer and the αB-crystallin/VEGF protein–protein interaction
  作者：Nelly A. Fosu-Mensah、Wen Jiang、Andrea Brancale、Jun Cai、Andrew D. Westwell

  DOI：10.1007/s00044-018-2275-9

  日期：2019.2

  Oestrogen receptor-negative breast cancer, particularly subtypes such as triple-negative breast cancer (TNBC, around 10-15% of cases), are characterised by poor long-term survival, poor response to therapy and early progression to metastasis. Purine-based compounds represent a privileged scaffold in anticancer drug design, with several clinically approved and experimental agents in clinical development comprising a purine core structure. In this study, a series of new purine-based compounds were synthesised; seven of the new analogues were found to significantly reduce the in vitro viability of TNBC cell lines (MDA-MB-231 and MDA-MB-436) with IC50 values of 50M. In previous work, we have proposed a new concept for targeting angiogenesis driving TNBC progression, by disrupting the protein-protein interaction between the molecular chaperone B-crystallin (CRYAB) and VEGF. Since previous clinical studies applying anti-VEGF therapy to TNBC patients have met with limited success, we were interested to test our most promising purine analogues against CRYAB/VEGF, using a custom-designed cell-based CRYAB/VEGF(165) interaction assay platform. Analogues 4e and 4f significantly reduced the interaction between CRYAB/VEGF(165), and compound 4e (100M) was also found to decrease the levels of soluble VEGF expressed by MDA-MB-231 cells by 40%. In conclusion, these promising early activity profiles warrant further investigation to validate this concept.
• CHARUSHIN V. N.; KAZANTSEVA I. V.; PONIZOVSKIJ M. G.; EGOROVA L. G.; SIDO+, XIMIYA GETEROTSIKL. SOED.,(1986) N 10, 1380-1388
  作者：CHARUSHIN V. N.、 KAZANTSEVA I. V.、 PONIZOVSKIJ M. G.、 EGOROVA L. G.、 SIDO+

  DOI：——

  日期：——
• GINER-SOROLLA A.; SEGARRA J. T.; BROOKS M. H., J. MED. CHEM., 1978, 21, NO 4, 344-348
  作者：GINER-SOROLLA A.、 SEGARRA J. T.、 BROOKS M. H.

  DOI：——

  日期：——